Senior Software Developer, Delivery Platform

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Wealthsimple

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2014

💼 Consulting

🛡️ Insurance

💳 Fintech

🔥 Funding within the last year

💰 $393M Series E - Wealthsimple on 2025-10

Consulting • Insurance • Fintech

Wealthsimple is a Canadian financial technology company that provides consumer banking, investing, and wealth management services. It offers chequing accounts, savings, credit cards, self-directed trading (stocks, ETFs, options), cryptocurrency trading, managed portfolios, tax services, and advisory wealth management for high-net-worth clients. Wealthsimple combines digital-first banking and low-fee investing products aimed at retail customers, along with tools and educational content to support personal finance.

📋 Description

• Evolve progressive delivery with Argo Rollouts and GitOps by enhancing canary deployment strategies, health checks, rollback triggers, and self-service deployment tools • Optimize CI/CD infrastructure, build times, artifact management, and package publishing workflows across hundreds of services • Design and implement deployment gates and guardrails, including end-to-end testing, load testing, and progressive delivery validations • Build deployment monitoring, dashboards, alerting, and visibility through Datadog, custom tooling, and Backstage • Drive Wealthsimple's reliability mission through chaos testing frameworks, automated rollbacks, and deployment confidence metrics • Partner with engineering teams to understand deployment pain points and build solutions that increase velocity • Share expertise through documentation, training sessions, and code reviews • Mentor mid-level engineers across the organization • Use metrics to establish baselines, set targets, measure impact, and guide technical decisions

🎯 Requirements

• 7+ years of experience in software development as part of a team, with significant experience in platform engineering, DevOps, CI/CD, or site reliability engineering • Deep expertise with Kubernetes, GitOps workflows such as ArgoCD, progressive delivery patterns, and CI/CD infrastructure at scale • Understanding of canary deployments, blue-green strategies, and automated rollback mechanisms • Experience designing, building, and maintaining CI/CD systems using Buildkite, GitHub Actions, Jenkins, GitLab CI, or similar • Ability to optimize build times, manage artifacts, and ensure pipeline reliability • Experience building observable systems with Datadog, Prometheus, or similar monitoring platforms • Understanding of SLIs, SLOs, error budgets, and measurable, resilient systems • Experience with TypeScript, Ruby, Python, Kotlin, or similar languages • Experience with AWS, Terraform, or similar infrastructure automation tools • Ability to build reproducible, version-controlled, and scalable infrastructure • Product mindset for internal platforms and ability to understand developer pain points and measure impact • Collaborative approach and passion for mentorship • Comfort presenting technical concepts to diverse audiences and building consensus across teams • Data-informed decision-making skills, including establishing baselines, setting targets, and tracking progress

🏖️ Benefits

• Top-tier health benefits and life insurance • Long-term group savings with employer match, through Wealthsimple for Business • 20 vacation days • 4 wellness days • Unlimited sick and mental health days per year • Work outside Canada for up to 90 days per year • Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS • Permanent employees receive equity compensation